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Synthesis of Functionalized 4,1‐Benzothiazepines via a [4+3] Annulation between Aza‐<i>o‐</i>Quinone Methides and Pyridinium 1,4‐Zwitterionic Thiolates

Chuan‐Chuan Wang, Xuehua Liu, Xinlu Wang, Huapeng Cui, Zhiwei Ma, De‐Gang Ding, Jun‐Tao Liu, Lei Meng, Yajing Chen

2021Advanced Synthesis & Catalysis30 citationsDOI

Abstract

Abstract The [4+3] annulation of aza‐ o ‐quinone methides and pyridinium 1,4‐zwitterionic thiolates has been developed for the one‐step synthesis of functionalized 2,3‐unsaturated 4,1‐benzothiazepines under mild and metal‐free conditions. The produced 4,1‐benzothiazepines can easily be converted into biologically interesting sulfoxides and sulfones via selective oxidization with m ‐CPBA. magnified image

Topics & Concepts

AnnulationPyridiniumChemistryQuinoneCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesSynthesis of Indole DerivativesCatalytic C–H Functionalization Methods
Synthesis of Functionalized 4,1‐Benzothiazepines via a [4+3] Annulation between Aza‐<i>o‐</i>Quinone Methides and Pyridinium 1,4‐Zwitterionic Thiolates | Litcius